# If you'd like to omit non-matching lines from the result; add ';d' to the end of the expression.
sed -E 's/(?<=\w)(?<!\w-\w)(?: ?-+ ?)+(?=\w)(?!\w-\w)/—/gm;t' <<< "<!-- The following should match. Not the dashes in the comment tag, obviously ;P -->
<h2 class=\"chapter_title\">Chapter 01 -- The Beginning</h2>
<h2 class=\"chapter_title\">Chapter 02 - The Reckoning</h2>
<h2 class=\"chapter_title\">Chapter 03 - - The Aftermath</h2>
<h2 class=\"chapter_title\">Chapter 04--The Conclusion</h2>
<p>I was having the usual - cheeseburger and a cold beer.</p>
<!-- The following should not match -->
<p>I was wearing a t-shirt.</p>
<p>It was a drunken mix-up</p>
<p>---</p>
<p>-----</p>
<p>- - -</p>
<p> - - </p>
<p> - - - </p>
"
Please keep in mind that these code samples are automatically generated and are not guaranteed to work. If you find any syntax errors, feel free to submit a bug report. For a full regex reference for SED, please visit: https://www.gnu.org/software/sed/manual/html_node/The-_0022s_0022-Command.html